There is a number of very surprising road signs in Russia. Some of them are related to the ring roads, which is a common phenomenon for cities that played a cornerstone role in logistics for a long period of time. From early years till now, all main roads of the European part of Russia end up in Moscow. The more the city has grown, the more demanding were the distant connections between radii. Today Moscow has several inner ring roads as well as two very long concrete ones running outside the city borders.
Speaking of the signs, on the way to the Third Ring Road (the inner one) one can find the signs that direct to the "left of Third Ring Road" or to the "right of Third Ring Road". This helps in case you know whether you approach the Third Ring from inside (from the city center) or outside (from the periphery). But if you are disoriented, lost in the big net of interlaced roads, then left or right does make little sense.
This gets even harder when you actually have to choose the left lane on the bisection while heading to the "right part of Third Ring Road".
Another example is related to the Moscow Automobile Ring Road (let us call it MKAD). Its length is over 100 kilometers, it has 10 lanes in total, and it is still one of the heavy crowded roads of the city. For the orientational purposes, MKAD is divided into four different segments: North, South, West and East. There are two sets of road signs, showing directions to MKAD-North and MKAD-South, or to MKAD-West and MKAD-East, depends on from what direction do you approach the road. It is much better than in the previous case, since one is able to correlate with a map and cardinal directions. However, if you are heading from North-West, would it be written "MKAD-South" or "MKAD-East"?